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[reaction: see text] The arylative cyclization of allenyl-aldehydes with aryl iodides and hexa-n-butyldistannane to form substituted cyclopentanols and cyclohexanols by tandem palladium-catalyzed carbostannylation and allylation was achieved under mild conditions.
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http://dx.doi.org/10.1021/ol025557t | DOI Listing |
Org Lett
August 2015
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
An efficient cyclization of N-tosyl-aniline tethered allenyl aldehydes and arylboronic acids catalyzed by cationic palladium complex is developed. This annulation reaction provides a convenient process for the synthesis of 3,4-cis-1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity and enantioselectivity.
View Article and Find Full Text PDFOrg Lett
March 2008
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan.
A Pd(OAc)2-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.
View Article and Find Full Text PDFJ Am Chem Soc
January 2008
Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan.
Chem Commun (Camb)
November 2002
Department of Chemistry and Lab for Metal-Catalyzed Reactions, Sungkyunkwan University, Suwon 440-746, Korea.
Highly stereoselective alkylative and arylative cyclization reactions of allenyl-aldehydes and -ketones with organozinc reagents occur efficiently in the presence of catalytic Ni(COD)2 to afford cis-fused homoallylic cyclopentanols.
View Article and Find Full Text PDFOrg Lett
November 2002
Department of Chemistry, Wayne State University, Detroit, MI 48202-3489, USA.
The direct cyclization of allenyl aldehydes with organozincs in the presence of Ni(COD)(2) provides synthetically versatile homoallylic alcohols. Both monosubstituted and 1,3-disubstituted allenes participate in the process, with the latter allowing preparation of stereochemically defined trisubstituted alkenes. [reaction: see text]
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